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45. John Candy

Before Jason Alexander was inadvertently setting trends as George Costanza, John Candy was already rotating a wardrobe of reliable menswear staples. Sure, it wasn't mind-blowing fashion, but it looked good, worked, and wouldn't look out of place today. He especially shined when he rocked a fedora, topcoat, and scarf. Oh, and that whole patterned shirt buttoned all the way up with no tie under a sportcoat look? Yeah, he started it.